Hydrochloric Acid → 3,5-Dichlorobenzoic acid

HRID 426925Notes

Reaction equation

HRID 426925 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:4]([C:5]([OH:7])=[O:6])[C:3]=1N.C(O)(C)C.Cl.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 760363,5-Dichloroanthranilic acidHCID 23668193Sodium Nitrite

Product 1

HCID 58113,5-Dichlorobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

206 parts of 3,5-dichloroanthranilic acid are introduced into 200 parts of isopropanol and 800 parts of 18 percent strength by weight hydrochloric acid. A solution of 100 parts of NaNO2 in 140 parts of water are run in at 80° C., resulting in the uniform evolution of nitrogen. The mixture is cooled, 500 parts of water are added and the product is filtered off. 182 parts (95% of theory) of 3,5-dichlorobenzoic acid of melting point 178°-180° C. are obtained.

Workup

  1. customare run in at 80° C.
  2. customresulting in the uniform evolution of nitrogen
  3. temperatureThe mixture is cooled
  4. filtrationthe product is filtered off

Sources & evidence

ORD record
ord-f213f3735aa44d5e8e0a6cebeedd4200
Source dataset
uspto-grants-1979_10
Patent number
US04172098

Reaction notes

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